Biography

I’m a truck driver, a father, a grandfather—and a man shaped by the road, by adversity, and by purpose.

I’ve raised four adult children and now have two grandchildren who remind me every day why legacy matters. My journey has taken me from boardrooms to backroads, from corporate finance to long-haul trucking, and from being taken hostage at gunpoint to finding deep freedom through faith, movement, and meaning.

In the early 1990s, at 23, I was a young urban professional—a “Yuppie”—when my life took a hard turn. I was taken hostage at gunpoint; it rocked my world and shattered my assumptions. That event triggered a lifelong pursuit of truth, clarity, and transformation.

Since then, I’ve:

• Run over 25 marathons

• Climbed multiple 14’ers in Colorado

• Backpack soloed the Camino de Santiago across Spain

• Hiked the North Country Trail across Michigan’s Upper Peninsula

• Traveled every U.S. state (lower 48) and most of Canada in a big rig

• Competed in a bodybuilding show in my 40s

• Performed in theater productions and musicals

• Ran for Michigan State Representative

• Built (and rebuilt) businesses

• Studied the Bible almost every day for decades

• Survived a divorce and came out better and stronger on the other side

I’ve worked as a stockbroker, banker, actor, Uber driver, and now own and operate Grey Cap Transportation, a hotshot logistics company born from a 2016 Uber ride with Post Malone—who thought my grey cap was “cool AF.” That moment sparked something. So did the dozens of passengers who kept asking, “Where can I follow your wisdom?”

That’s how Trucker Dad was born.

I’ve authored three books (with more on the way), and I’m passionate about helping people wake up, take charge, and live on purpose with a mission of their own. I’m not here to sugarcoat life or feed you hype. I’ve been through real stuff. I’ve won. I’ve lost. I’ve learned.

And I believe your life—just like mine—isn’t random. It’s a story being written every mile, every morning, every moment you choose truth over comfort.

If you’re looking for authenticity, perspective, and purpose—you’re in the right place.

Start your engine and let’s roll.



- Robert Regan, Trucker Dad